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What Would You Do?

In the 1970s, I was a backgammon player in Los Angeles. Decent enough player, but not great.

One of the semi-regular players at the Cavendish West was a guy named Steve. Steve was a so-so intermediate player — but he cheated. After a while, word got out and he couldn’t get into a game because his reputation preceded him.

I didn’t mind him as a person, although I would never gamble with him nor ever enter into a deal with him where he had a chance to screw me. Our respective girl friends liked each other and sometimes we went out as a foursome. I always insisted on him giving me $100 before we went out to cover his half of the meal. I would return any amount left over. No $100 beforehand meant no double date.

In January 1977, we visited a restaurant that I liked and Steve had never visited. It was a week before the Oakland Raiders versus Minnesota Vikings Superbowl XI. Since the game was being held in nearby Pasadena, there was a lot of local interest and the owner/cook, Jack, had the restaurant decorated in silver and black — signifying he liked the Oakland Raiders in that game.

Steve saw an opportunity. He was quite a charming guy — until it became time to pay up. He chatted up Jack and before too long they made a bet for “double or nothing for the next meal Steve ate” based on the results of the upcoming game.

Although the bet sounded fair, knowing Steve, it clearly wasn’t. If the Vikings won, Steve would bring three guests and order up lobster tails all around with several bottles of expensive wine. If the Raiders won (which actually turned out to be the case), Steve would disappear. He would never be around to pay off the bet.

By accepting the bet, Jack put himself into a position where he couldn’t win, but he could lose big-time. 

My personal philosophy on bets between two other people is to stay out of it unless a family member was taking the worst of it. Whatever the two of them arranged was fine. Even if I thought one of them was taking the worst of it, I kept my mouth shut.

And that’s what I did here — with great misgivings.

While I didn’t know Jack well, I had been there for dinner three or four times and we greeted each other by first names. He didn’t know Steve was a sleazeball, but I did. Did he have a reasonable expectation that I wouldn’t bring someone dishonorable into his restaurant? I wasn’t sure, but it didn’t feel right to me.

Since the Raiders ended up winning, that was clearly the “least bad” result for Jack. He wasn’t going to get paid off by Steve, but his team won, and he wasn’t going to be out anything. 

Even so, I didn’t feel comfortable going back to that restaurant again. I didn’t want to answer questions about “my friend Steve and when was he coming by to pay up.” So, I guess Jack did lose one occasional customer and one occasional friend.

What would you have done? Would you have spoken up at the time? And if so, would it have been in front of both of them or just privately with Jack? Keep in mind that the fact that the Raiders ended up winning is irrelevant to whether I should have spoken up at the time of the bet. When it was time to “do something or not,” the game had not yet been played.

Author’s Note: I recently broke my rule about not getting involved if a family member of mine was taking the worst of it. There was a Caesars Seven Stars party and I got tickets for Bonnie, her sister, and her daughter. I was off at an Improv workshop. The three ladies would have a good time together.  Bonnie had met several of my gambling friends that she liked and many of them would probably be there.

During the evening, Bonnie ran into two of these friends, “Tim” and “Alice.” Tim talked Bonnie into a $3 bet on an upcoming football game. Bonnie came back and told me about her bet with Tim, but she had no idea what team she bet on. She couldn’t tell me which teams were playing, let alone who was favored. Tim sent an amusing email contract using over-the-top legalese documenting the bet. I accepted on Bonnie’s behalf and promised to hold her feet to the fire should she lose.

Turns out that Bonnie’s team was a 1½-point underdog and she was making the bet straight up. While she’s definitely a family member taking the worst of it, I kept quiet. For $3 at a time, getting the wrong side isn’t so terrible.

15 thoughts on “What Would You Do?

  1. In my opinion, you were in the wrong. You knew Steve was, in all likelihood, freerolling Jack. Gamblers live and die by their word and their reputation. Being associated with a freeroller will likely negatively affect your reputation nearly as much as being a freeroller yourself. This is compounded by the fact that Jack is a square and, from what you state in your story, seemingly a good person. If it were two scumbags or two pros trying to outwit each other, I think staying out of it is more justifiable.

    I once had a friend who was being staked in some big poker games by a pro with whom I was on bad terms. He quickly fell deep into makeup. He asked me about the prospect of just cutting and running, and I told him that if he did, I would have to disassociate myself from him completely. People can like me or dislike me, but if someone questions my word, then I have a problem. And to avoid that, it is best to be beyond even the companionship of dishonesty.

  2. I would’ve disassociated myself from him eight steps before that. He’s a cheat and a sleaze ball, to the point where you can’t even trust him to pay you back for his half of a joint dinner. So why would you want to go out to dinner or be friends with this guy or spend any time around him in the first place. You can’t be half a sleaze ball. If you’re a sleaze ball in one aspect of your life, then you’re a sleaze ball, period. A guys who’s a nice guy half the time and a sleaze ball half the time is 100% sleaze ball. I would’ve found some better friends and certainly never introduced him to anyone I knew, even someone as casual as the owner of the restaurant I ate in a few times. I cut crappy people out of my life.

  3. Steve is and was the worst kind of friend. A known cheat who probably sold used cars for a living. The best thing you could have done is had nothing to do with him – then you would not have found yourself in this dilemma.

  4. By not ever returning to the restaurant again, Jack could take it that you were in league with Steve. Or Jack could take it that you were too embarrassed to keep doing business there, reinforcing his perception of your alliance with Steve. You blew the opportunity to just walk in and be straight up about things, patronizing the place supporting Jack in this way. As for the possibility of being asked by Jack when Steve would be returning to pay up, you suspected never but certainly didn’t know for certain, and that’s all you would have to say, you had no idea. Jack let himself be suckered into the bet which was too bad but not on you. I don’t think you had an obligation to advise Jack..

  5. I may be inferring too much from your story, but I get the impression that you didn’t know Jack all that well. How confident are you that he would give Steve carte blanche if he lost the bet? Do you know that he wouldn’t have said, “Anything you want on the house – as long as it’s under $20”?

    It’s also unclear to me what “double or nothing” means in this context. Did they agree that Steve would return and pay twice the going rate for a dinner? Or just that he’d come back and buy dinner as a customer? In either case, Jack may have been looking at this as low-cost advertising. Unless I’m completely misreading this situation, I think you were right to stay out of it.

  6. Interesting topic, Bob.

    I agree with Houyi’s comment. Getting the best of it is different than outright cheating, and you never want to be associated with cheating.

    A tougher call would have been if you knew Steve was actually going to “pay up”, but still would get the best of it by ordering extravagantly if he won the bet, while ordering cheaply if he lost. And what about a case where Steve would order the same dinner, win or lose, but the Raiders were 14-pt underdogs, and Jack was taking them straight up?

  7. Bob,

    You are judged by the friends you keep and the friends you keep away from. If I have an interaction with Person A and Person A is friends with Person B, who is less than scrupulous, I am more cautious in my dealings with Person A. Person A is free to choose his friends and I am free to use that information in how I deal with Person A.

    One solution might have been to say ” why don’t you put a cap on the dinner charge?”. Or if you really wanted get involved, you could have offered to hold x dollars from each of them and you would settle up after the wager.

    I had an interesting exchange with someone on vpfree. This person thought that if someone was pushed overboard on a cruise ship and I did nothing to save him, I was as much at fault as the person who pushed him. I disagreed. His point was that either way, that person was probably going to die and each us contributed to his death. I disagreed but understand that I might have some responsibility. Many factors in this example but the issue is one worth discussing. What is your obligation if you know something bad is going to happen to someone? More of an ethical than legal question.

    Back to your situation, I would be a little less likely to do business with you after this incident. It’s not a moral judgement but it tells me that you might not always be acting in my best interest in a given situation. It also tells me that if the business dealing between us isn’t clearly spelled out and there is an occurrence that is open to debate, you might not be committed to doing the right thing. This happens a lot on gambling partnerships. I very rarely partner with people for any significant money unless I trust they will do the right thing in a gray area event and I am comfortable that if they gray area decision goes against me, the money won’t be a big loss. I have seen way, way, way too many gamblers ( and people in general) do crazy stuff for a few dollars.

    I am also confident you would handle the situation differently today.

  8. Bob you made a mistake.

    Not by not telling Jack about Steve, but by staying Steve’s friend even after you knew he was gambling scum. I don’t care how nice a guy someone is, if I can’t trust them, why would I continue to keep them as a friend?

  9. I think what everyone is ignoring here is that the respective girlfriends were friends, not really Bob and Steve, but Bob went out to dinner with Steve because of the relationship (AND protected himself by getting the money up front). I DO agree that he should have gone back, if nothing else to defend himself and assure Jack that he wasn’t a party to the shenanigans, and that Steve was not a friend. He also could have called Steve and said “So, when are we going back to the restaurant for the meal on you to pay off the bet?”

  10. You knowingly went out with a guy you knew was a thief and a cheat, plus couldn’t rely on him paying his fair share. What were you thinking?

  11. Bob,
    This happened in the 1970’s? That’s a long time to have “misgivings”.
    If Jack is still living, fix it.

  12. Guilt, the gift that keeps on giving. LOL.

  13. While I don’t think I would have called out Steve, I probably would have injected myself into the conversation and discouraged a bet being made in the first place. Any excuse would have been good.. even a lame one, so that perhaps Jack could read between the lines. There might have been some subtle eye movements to go with it.

    The one thing you mentioned, Bob, that I thought was odd was the requirement that he give you $100 up front for the night and you’d pay him back HIS money that he didn’t spend at the end of the night. I couldn’t ever imagine doing that with a friend or acquaintance. ie: if I felt the need to do that with someone, I wouldn’t go out with them in the first place.

  14. Shame on you Bob. You knew about this guy being a total degenerate and you still hung out with him because his girlfriend and your girlfriend liked each other. It didn’t matter that your girlfriend or whoever wanted to go out for dinner back then as a foursome. You should have spoke up and told Steve and his girlfriend that you already had plans. That way you wouldn’t have the grief and guilt on your conscience of the restaurant owner getting fucked over by Steve, come to find out. A guy like that is always looking for an angle to get over on someone and he helped to ruin your reputation at that restaurant as you mentioned that you never returned to it. So what Steve did affected you, but you allowed it to happen.

    Another thing, when you go out to dinner don’t needle a person beforehand and ask them for $100. That is so embarrassing and lacks class. If you have to do that then you shouldn’t be going out to dinner with the guy in the first place. Either pick up the tab yourself or make sure that he has enough to pay for him and his girl before you go. Overall you stuck to your own word on not getting involved in the bet between the two guys.

  15. Was it Steve Wynn?

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